Palladium-catalyzed Suzuki cross-coupling of aryl halides with aryl boronic acids in the presence of glucosamine-based phosphines

Kołodziuk, Robert; Penciu, Alexandra; Tollabi, Mustapha; Framery, Éric; Goux‐Henry, Catherine; Iourtchenko, Alexander; Sinou, Denis

doi:10.1016/s0022-328x(03)00636-3

Cited by 27 publications

(16 citation statements)

References 13 publications

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“…These ligands display higher partitioning into the organic phase of a water/di-n-butyl ether/ethanol solvent system at 50 ˚C (0.117), compared to room temperature (0.086). 3) gave catalysts that provided modest to excellent yields for the Suzuki coupling of activated aryl iodides and bromides in a toluene/aqueous ethanol solvent mixture [115,116]. Ligands derived from the glycosylated phosphines were also active for the Heck coupling of aryl bromides at 130 ˚C.…”

Section: Neutral Hydrophilic Triarylphosphinesmentioning

confidence: 99%

Palladium-Catalyzed Cross-Coupling in Aqueous Media: Recent Progress and Current Applications

Shaughnessy¹,

DeVasher²

2005

COC

181

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Water has attracted significant attention as an alternative solvent for homogeneous metal-catalyzed reactions because it is a non-toxic, nonflammable solvent that can allow for simplified recovery of homogeneous catalysts. The use of water as a solvent in palladium-catalyzed cross-coupling reactions is of great academic and industrial interest. Palladium-catalyzed coupling reactions are powerful methods to make carbon-carbon and carbon-heteroatom bonds under mild conditions. Separation of the catalyst from the organic product can be very difficult; however, constraining the catalyst to the aqueous-phase of an aqueous-biphasic solvent system can potentially simplify catalyst recovery. This review will focus on recent developments in the design and application of aqueous-phase, palladium-catalyzed coupling reactions over the period from 2000, through late 2004. A variety of new hydrophilic ligand architectures have been introduced recently that provide significantly more active catalysts towards industrially relevant aryl bromides and chlorides. Stille CouplingRSiX3 L n Pd(Cat) Hiyama Coupling

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Section: Neutral Hydrophilic Triarylphosphinesmentioning

confidence: 99%

Palladium-Catalyzed Cross-Coupling in Aqueous Media: Recent Progress and Current Applications

Shaughnessy¹,

DeVasher²

2005

COC

181

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“…Scaffolds on which these groups are usually placed are the phenyl ring, but there are examples of heterocyclic compounds and metallocenes. These ligands, which can be depicted by a general formula I , work with various metals, for example, palladium , rhodium , copper , and iridium (see Fig. ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Precursors of 4‐Phosphino‐1H‐pyrrole‐3‐carbaldehyde Derivatives

Smaliy

Chaykovskaya

Shtil

et al. 2013

Heteroatom Chemistry

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“…18 These ligands could be afforded from either protected or unprotected D-glucosamine. The synthetic pathway to the glucosamine-based phosphine ligands is shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

“…In 2003, Sinou and co-workers reported a class of easily obtainable phosphine ligands bearing a carbohydrate skeleton. 18 These ligands could be afforded from either protected or unprotected D-glucosamine. The synthetic pathway to the glucosamine-based phosphine ligands is shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

The Recent Development of Phosphine Ligands Derived from 2-Phosphino-Substituted Heterocycles and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions

Wong¹,

So²,

Kwong³

2012

Synlett

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Heterocyclic phosphines have long been used as unique and efficient ligands for palladium-catalyzed cross-coupling reactions. The simplest ligand, trifurylphosphine, has become one of the most classical heterocyclic phosphines for coupling reactions since its first application in the Stille coupling reaction in 1988. In recent decades, palladium catalyst systems derived from highly diverse and innovative heterocyclic phosphines have shown excellent catalytic activities in cross-coupling reactions. In this account, we discuss the recent development and applications of heterocyclic phosphine ligands, highlighting the synthetic pathways used to prepare the ligands. The sections are categorized by the different palladium-catalyzed cross-coupling methodologies.

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Palladium-catalyzed Suzuki cross-coupling of aryl halides with aryl boronic acids in the presence of glucosamine-based phosphines

Cited by 27 publications

References 13 publications

Palladium-Catalyzed Cross-Coupling in Aqueous Media: Recent Progress and Current Applications

Palladium-Catalyzed Cross-Coupling in Aqueous Media: Recent Progress and Current Applications

Synthesis of Precursors of 4‐Phosphino‐1H‐pyrrole‐3‐carbaldehyde Derivatives

The Recent Development of Phosphine Ligands Derived from 2-Phosphino-Substituted Heterocycles and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions

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